The Leafs arn't in such a bad shape at all, Shanahan just needs to show he's got the balls to make moves.
The Leafs have a good base core. They have Rielly, Nylander, Bernier, Percy, Gauthier, Gardiner, JVR, Komarov, Holland, Panik, Kadri. If you can find a suitor for Kessel, you're getting at least a key young player back + a 1st round pick.
Clarkson needs to go to the minors. Then, Bozak dumped for a pick or two, and Phaneuf for a decent return if possible.
The Leafs would be left with a so-so roster, but some very good young players. They're also gonna have a high pick in 2015, and probably again in 2016.
From then on, they should enter a window in which they'd be considered one of the top up-and-coming teams around, if Shanahan doesn't screw up. They'll also possess one very hot commodity these days: cap space.
Leafs skeleton:
Van Riemsdyk - Nylander - ??
2015 1st - Kadri - 2016 1st
Komarov - Gauthier - UFA
McKegg/Carrick - Holland - Panik
Rielly - ??
Gardiner - Finn
Percy - Granberg
Bernier - UFA
This is not a rocket science roster, basically just sign one or two UFA for depth and what really needs to be done is finding another potential front-line player either a F or a D via the Kessel trade... Then just get as much assets as possible from trading the likes of Lupul, Franson, Phaneuf, Winnik, Santorelli, Reimer and Bozak and the rest should play itself out with good player development and smart moves by Shanahan. Draft well and and developp well, that's they key.